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241512

Sigma-Aldrich

Tetrabutylammonium fluoride hydrate

98%

Synonym(s):

TBAF

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About This Item

Linear Formula:
[CH3(CH2)3]4NF·xH2O
CAS Number:
22206-57-1
Molecular Weight:
261.46 (anhydrous basis)
MDL number:
MFCD00149980
UNSPSC Code:
12352116
PubChem Substance ID:
24854487
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

mp

62-63 °C (lit.)

SMILES string

O.[F-].CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.FH.H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;;/h5-16H2,1-4H3;1H;1H2/q+1;;/p-1

InChI key

UQCWXKSHRQJGPH-UHFFFAOYSA-M

General description

Tetrabutylammonium fluoride hydrate is known to be a source of F− anion, used in nucleophilic fluorination reactions.

Application

Reactant for preparation of:
  • Double clathrate hydrates at high pressures
  • Cellulose ethers
  • Terminal olefins via dehydrohalogenation reactions
  • Neutral and zwitterionic 3-carboranyl thymidine analogues for boron neutron capture therapy
Tetrabutylammonium fluoride hydrate can be used:
  • To prepare 2,7-diethynyl-9-propyl-9H-carbazole, which is a key intermediate for the synthesis of calix[4]arene−carbazole polymers.
  • As an anion source in the study of selective detection of F− by anion receptor viz Schiff base.
  • To prepare terminal olefins from primary alkyl iodides

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN7855
SHBN3247
SHBM7805
SHBJ2920
SHBG9972V

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Naked-eye detection of F- and AcO- ions by Schiff base receptor
Dalapati S, et al.
Journal of Fluorine Chemistry, 132(8), 536-540 (2011)
Synthesis, 3085-3085 (2006)
Calix [4] arene-carbazole-containing polymers: Synthesis and properties
Barata PD, et al.
Reactive and Functional Polymers, 72(9), 627-634 (2012)
Hydrated tetrabutylammonium fluoride as a powerful nucleophilic fluorinating agent
Albanese D, et al.
The Journal of Organic Chemistry, 63(25), 9587-9589 (1998)
Sílvia Santos Pedrosa et al.
Macromolecular bioscience, 16(11), 1610-1620 (2016-07-28)
Hyaluronic acid nanogel (HyA-AT) is a redox sensitive crosslinkable nanogel, obtained through the conjugation of a thiolated hydrophobic molecule to the hyaluronic acid chain. Engineered nanogel was studied for its biocompatibility, including immunocompatibility and hemocompatability. The nanogel did not compromise
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